Azo dyes.



diazo compound with an aminonaphthol ex'yoztrlmxylic acid.

- riireur orricie lie-resi ns KUTEHE, or VOHWINKEL, NEAR ELBERFELD, ANDOSCAR DRESSEL, or

ELBERFELD, GER-MANY, ASSIGNORS '10 SYNTHETIC PATENTSCQ, INQ, OF

NEW YQEK, N. '35., A CORPORATION OF HEW YDRK AZO EYES.

:5 hrswlugv T all re/5.0m it may concern Be known that We, RlCHARD KOTHEand AR Denssnn, doctors of philosophy, citizens of the German Empire,residing at Vohvinkel, near Elloerfeldy and lfilherfeld, Germany,respectively, have invented new and. useful Improvements in Azo Dye-s,of whichthe following is a specification.

ive here found that new and valuable also dyestufl'scan' be obtained bycouplinge coz 'ipound in which the amino group is substituted by aresidue of a sullonyl-ortho- 'l'hc new coloring matters dye wool froinon acid bath in orange to moletfpure shades which. after-treated withchromates change into ol'uer tints remarkable for their excellentiss'tness to milling and Washing. Theyare off-or being dried andpulverized generally from reddish to hrownishq'ed powders soluble inwater and in concentrated sulfuric acid generally With a reddish tobrownish-eolornti'on. Theyield upon reduction with stannous chlorid andhydrochloric iicid aromatic amino compound and a diuminonephthclderivative which contains in one amino group it residue of asulionylphenolcorhoxylic acid.

in order to illustrate the new process more fully th following exampleis given,

the parts being by weights:-9.3 parts of 53"lil31 ore diezotized with6.9 parts of souin nitrite and 8 ports .othydrochloric r. id and thedinzo solution is'iidded while log stirred to a solution of 52 parts ofthe uroduct obtained from the sulfonylchlorid salicylic acid and1.S-omin0naphthol- 3.G-disulfonic acid:

' SOz- OH H H- l l A containing soda in excess. When the diezocompoundcan no longer to he proved to he in the inixtur the dyestull' is saltedout, filtered of? and dried. lit yields on wool-from an acid both purered shades, titer chromed :.hey are bluer Very fast to Washing and tomilling. Printed on cotton with COOH Specification of Letters Patent.

Application filed January 5, 191.4. Serial No. 810.471.

late of chromium :1

, fon l 1,7-eminonuphthol,

Patented Jan. 26, TIME.

pure bluish-red very fast to Washing is obtained. '1 he new dye .isafter 'beingdried and pulverized in the shape of its sodium salt areddish powder. soluble 111 Water and in concentrated sulfuric acid with:1 reddish coloration. Upon reductionwitn stennous ClllUl'ld andhydrochloric acid anilin and salicylsulfmiyl-LT-diamino-8-naphthol-3Xi-disulfonic :icid are obtained. It has in a freestate the formula:

diphenylurea, l naphthylzunin 4 sulfonic acid, l-nuphthylmnin-5-sulfonicacid, the intermediate compound from 'hen'zid-in and salicylic acid,etc. In the some way other of the ahoye mentioned amino-naphthol compounds inay he used such 41s sulicylsul I solic vlsulfonyl- 2.7aminonaphthol, sulicylsulfonyl 1.5- uninonaphthol-Tesulfoni-c. acid,sulicylsulfonyl 7 1.8 -.an'1inonnphthol -l sul'fouic acid,

sulicylsul-fonyl 1.8 :uninomiphthol (l sul ionic acid.shlicylsu-lfonyl-Q.S-aminonaphthol lksulfonic a cid salicylsulfonyl-2.8-aminonophthol-(i-sulfonic acid. ortho-crcsotin -sul'fon vl 1.8aniinonaphthol =31 disulfonic acid derived from the cresotin sulfonicacid, of the followiii-g formula:

sulfonic acid etc.

We clonnzl. The new ezo dyes which are after being dried and pulverizedgenerally from reddish to brownislrrcnlpowders soluble in Water and 1Hconcentrated sulfuric acid generally with a reddish to brownish-red clorotion,

yielding upon reduction with stannous chloridcnd hydrochloric acid anaromatic amino compound. and. c (lioxninonnphthol dcri'voti've tintsremarkable for their excellent ifnstncss v to milling and washing,substantially as ole-- scribed.

' 2. The new one dyes which creditor hcino dried and pulverizedgenerally from reddish to orowinsh-red powders soluble in water end inconcentratedsulfuric cold generally with e reddish. to brownish-redcoloration,

yielding; upon reduction with stsnnoue chlo= rid and h drochloric a 'don crcnmtic amine compound and. u disc .nonophthol sulionic acid whichcontains in one amino group at residue of c suli'onylphcnolcerhoxylicacid cnddyeing wool from an acid bath gencu ally from orange to violetpure shades "which oiter treated with chromotes. change into hluer tintsifiil'litllidlflle for their excellent fustness to milling and washing,substantiolly as described.

3. The new ezo dyeswhich after being; dried end'pulverized generallyfrom reddish to brownish-red powders soluble in water and inconcentrated sulfuric acid genera ly With e reddish to brownish-redcolore i I yleldihg upon reduction with stennous chlo- .ricl and hdrochloric acid an aromatic amino componn end a diarrrinoncyjhtholderivative which contains in one amino group a sclicylsulfonyl residueand dyeing wool from on acid bath gencrall iirom orange to violet pureshades which a tor mates change into hlucrftints remarkable for theirexcellent fastness to milling and washing substantially as described.

l. T he new azo dyes which are dried and pulverized generally fromreddish to brownish-red powders soluble in water and in conc'cntrutedsulfuric acid generally with o reddish to brownish-rod colorctionyielding upon reduction with stannous chlorid end-hydrochloric acid anaromatic amino compound and n dicminonuphthol sulfonic ccidwhich'contziins in one amino group a 'solicylsulfonyl -from on acid hathgenerally from orange to Violet pure shades which after treated with'chromctes change into'bluer tints rezncr able for their excellent icstnc s's to milling andwushing, substantially as described.

5. The new azo dyes which are after being i 1.\ \NW treated withchr-oafter being resiclue and dyeing wool i scribing witnesses.

dried and pulverizcd generally from reddish to hrownlsh-red powderssoluble in water and in concentrated sulfuric acid generclly'with I ereddish to brownish-red coloration, yield ing npcn-rcductionwith o.stonnous chlorid and hydrochloric acid an aromat c mi'no compound and ndmnnnonophthol disu ionic acid-which contains in one amino group aresidue of e solfonylphcnolcorboxylic' acid end dyeing wool from an holdboth genorally from orange to violet pure shades 4 which. after treat-edwith chro nates change into loluer tints remarkable for their excellentfsstness to milling and washing, substantially as described.

The new azo dyes which are after hein dricd o-nd pulverized generallyfrom reddis to-hrownish-red powders soluble in wcter and inconcentrated. sulfuric acid generally witirc reddish to brownish-redcoloration, yielding upon cduction with stennous chlo-' ri'd andhydrochloric acid on aromatic amino compound d mnznoncphthol d1sulioiucacid which contains in one aminocoon I which dye is after heingdried andpulverized in the shape of its sodium stilt a reddish powder trz tedsulfuric acid with a reddish colorstreated with chromates 'changeinto 2rbluer shade remarkable for its excellent festness tomilling and,washing, substantially as dewv scribed.

in testimony whcrcoi' we'hcve hereunto sctour. hands in the presence oftwo sub- RICHARD KQTH OEaCAR DRESSEL.

Witnesses:

Ermine!) BAUjVI-HOEE Wi mer: Assoc.

dye having in a free state. most PTOl'ifibly the following generalformula:

soluble in water and in concenfies seeiions in Lefiere Faient No.i,i26,489.

after the word which insert the word wre' same a e I 1 g a It is herebycertified tha t in Letters Patent No. 1,126,489, granted January 26,

1915, upon the a l'ieatib'ifof Richard Kothe, of Vohwinkel, nwElberfeld, and

Oscar Dressel, of Elbez fek l, Germany, for an improvement in Azo Dyes,errors appear in the printed specification yequir ing correction asfollows: Page 2, fine 31,

line 90, for the word fl-om" read for, and line 107, for ehe article anread and; and thah the said Letters Patent should be read with thesecorrections hherein, that the same may con form to the record of thecase in the Patent Ofifice.

Signed and sealed this 13th day of April, A. D., 1915.

[em/uh] J. T. NEWTON,

Aviing Commissioner of Patents.

